Bailey Island Vacations 2026

Top Bailey Island hotels deals

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free cancellation

CA $158

CA $174 total

Jun 14 - Jun 15

includes taxes & fees

Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and State Theatre are located nearby.

Portland Harbor Hotel

468 Fore Street Portland ME

Free cancellation

Reserve now, pay when you stay

CA $394

CA $489 total

Jun 14 - Jun 15

includes taxes & fees

Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

Free cancellation

CA $336

CA $410 total

Jun 14 - Jun 15

includes taxes & fees

Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.

Portland Regency Hotel & Spa

20 Milk Street Portland ME

Free cancellation

Reserve now, pay when you stay

CA $354

CA $392 total

Jul 1 - Jul 2

includes taxes & fees

Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Free cancellation

Reserve now, pay when you stay

CA $137

CA $149 total

Jun 14 - Jun 15

includes taxes & fees

Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby.

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME

Free cancellation

CA $130

CA $142 total

Jun 14 - Jun 15

includes taxes & fees

Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's Point are located nearby.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Bailey Island Bridge

Find out about the history of Bailey Island when you spend time at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.

Cobwork Bridge

You can find out about the history of Bailey Island when you stop by Cobwork Bridge. Stroll along the seaside or seek out the hiking trails.

Land's End Gift Shop

Enjoy an outing to Land's End Gift Shop during your stay in Bailey Island. While you're in the area, find time to visit its shops.

Frequently asked questions

How much are vacation packages to Bailey Island?

Vacation packages, which provide both flights and hotels in Bailey Island, start at just . Make your travel fantasies come to life and secure your vacation with Travelocity today.

Where can I get the best vacation package deals for Bailey Island?

With around 400 partner airlines and 1,000,000 properties across the globe, you can't beat Travelocity. Browse our comprehensive range and score an incredible Bailey Island package deal. Don't you love it when travel is that easy?

Why should I book my Bailey Island vacation bundle with Travelocity?

With exceptional service, customer support available 24/7 and some of the most perfect escapes on offer, you'll never wander alone. And if you find a better price, we'll match it. That's our Price Match Guarantee.

Can I save money on my Bailey Island car rental if I bundle it with my hotel or flight?

Bundling your bookings into a Bailey Island vacation package will leave you with a nice chunk of spare change. You can bundle a car and flight; a hotel, flight and car; or a hotel and car. You won't find a better way to explore the greater Bailey Island region than with your own ride. You can also add experiences and tours to your Travelocity package.